organic compounds
of 3-hydroxymethyl-1,2,3,4-tetrahydroisoquinolin-1-one
aDepartmento de Física, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, bDepartmento de Química, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, cEscola de Engenharia de Lorena - EEL, Universidade São Paulo, SP, Brazil, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: ignez@ufscar.br
In the title compound, C10H11NO2, two independent but virtually superimposable molecules, A and B, comprise the The heterocyclic ring in each molecule has a screw-boat conformation, and the methylhydroxyl group occupies a position to one side of this ring with N—C—C—O torsion angles of −55.30 (15) (molecule A) and −55.94 (16)° (molecule B). In the crystal, O—H⋯O and N—H⋯O hydrogen bonding leads to 11-membered {⋯HNCO⋯HO⋯HNC2O} heterosynthons, involving three different molecules, which are edge-shared to generate a supramolecular chain along the a axis. Interactions of the type C—H⋯O provide additional stability to the chains, and link these into a three-dimensional architecture.
Keywords: crystal structure; hydrogen bonding; conformation.
CCDC reference: 1409827
1. Related literature
For background, including medicinal potential, to compounds related to the title compound, see: Biaggio et al. (2007); Grunewald et al. (1999); Zoretic & Soja (1977). For additional see: Cremer & Pople (1975).
2. Experimental
2.1. Crystal data
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2.3. Refinement
Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2014 (Burla et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMOL (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 1409827
https://doi.org/10.1107/S2056989015012670/hg5449sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015012670/hg5449Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015012670/hg5449Isup3.cml
Referring to Fig. 1, the treatment of lactam carbonate (1) with sodium hydride to form compound (2) was unsuccessful and led only to the lactam alcohol product (3). Compound (3) might be used as an intermediate in organic synthesis. The heterocyclic ring has a screw-boat conformation with puckering parameters (Cremer & Pople, 1975): Puckering Amplitude (Q) = 0.4213 (14) Å, θ = 64.15 (19)° and φ = 271.6 (2)° (molecule A), and Q = 0.4050 (15) Å, θ = 64.9 (2)° and φ = 269.3 (2)° (molecule B).
A 60% suspension of sodium hydride in mineral oil (22 mg, 1.55 mmol) was suspended in dry tetrahydrofuran (10 mL; THF) under argon. Lactam carbonate (1) (250 mg, 1.0 mmol) dissolved in THF (7 mL) was added drop-wise over 5 mins. The resulting reaction mixture was stirred at room temperature for 6 h. The solvent was removed with a rotary evaporator, and the resulting mixture was poured into saturated ammonium hydroxide (10 mL) and extracted with three 20 mL portions of chloroform. The chloroform extracts were combined and washed with saturated NaCl solution (20 mL), and dried over anhydrous Mg2SO4. The solvent was removed and the residue was purified by flash δ 7.20-8.00 (m, 4H, ArH), 7.70 (s, 1H, NH), 2.0-5.0 (m, 5H), 2.02 (s, 1H, OH). 13C NMR (300 MHz): δ 167.0, 137.9, 132.3, 126.0, 127.0, 128.0, 129.0, 65.0, 53.0, 30.0. IR (KBr, cm-1): ν 3684 (OH), 3399, (NH), 1667 (C═O).
(silica gel) with EtOAc as the to yield lactam alcohol (3) as a white solid (0.12g, 67%), which was slowly recrystallised from its chloroform solution (ca 7 days). M.pt: 140-142 °C. 1H NMR (300 MHz, CDCl3):Crystal data, data collection and structure
details are summarized in Table 1. Carbon-bound H-atoms were placed in calculated positions (C—H = 0.93 to 0.99 Å) and were included in the in the riding model approximation, with Uiso(H) = 1.2–1.5Ueq(C). The O-and N-bound H-atoms were refined with O—H = 0.84±0.01 Å and N—H = 0.86±0.01 Å, and with Uiso(H) = 1.5Ueq(O) or 1.2Ueq(N).Referring to Fig. 1, the treatment of lactam carbonate (1) with sodium hydride to form compound (2) was unsuccessful and led only to the lactam alcohol product (3). Compound (3) might be used as an intermediate in organic synthesis. The heterocyclic ring has a screw-boat conformation with puckering parameters (Cremer & Pople, 1975): Puckering Amplitude (Q) = 0.4213 (14) Å, θ = 64.15 (19)° and φ = 271.6 (2)° (molecule A), and Q = 0.4050 (15) Å, θ = 64.9 (2)° and φ = 269.3 (2)° (molecule B).
For background, including medicinal potential, to compounds related to the title compound, see: Biaggio et al. (2007); Grunewald et al. (1999); Zoretic & Soja (1977). For additional
see: Cremer & Pople (1975).A 60% suspension of sodium hydride in mineral oil (22 mg, 1.55 mmol) was suspended in dry tetrahydrofuran (10 mL; THF) under argon. Lactam carbonate (1) (250 mg, 1.0 mmol) dissolved in THF (7 mL) was added drop-wise over 5 mins. The resulting reaction mixture was stirred at room temperature for 6 h. The solvent was removed with a rotary evaporator, and the resulting mixture was poured into saturated ammonium hydroxide (10 mL) and extracted with three 20 mL portions of chloroform. The chloroform extracts were combined and washed with saturated NaCl solution (20 mL), and dried over anhydrous Mg2SO4. The solvent was removed and the residue was purified by flash δ 7.20-8.00 (m, 4H, ArH), 7.70 (s, 1H, NH), 2.0-5.0 (m, 5H), 2.02 (s, 1H, OH). 13C NMR (300 MHz): δ 167.0, 137.9, 132.3, 126.0, 127.0, 128.0, 129.0, 65.0, 53.0, 30.0. IR (KBr, cm-1): ν 3684 (OH), 3399, (NH), 1667 (C═O).
(silica gel) with EtOAc as the to yield lactam alcohol (3) as a white solid (0.12g, 67%), which was slowly recrystallised from its chloroform solution (ca 7 days). M.pt: 140-142 °C. 1H NMR (300 MHz, CDCl3): detailsCrystal data, data collection and structure
details are summarized in Table 1. Carbon-bound H-atoms were placed in calculated positions (C—H = 0.93 to 0.99 Å) and were included in the in the riding model approximation, with Uiso(H) = 1.2–1.5Ueq(C). The O-and N-bound H-atoms were refined with O—H = 0.84±0.01 Å and N—H = 0.86±0.01 Å, and with Uiso(H) = 1.5Ueq(O) or 1.2Ueq(N).Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR2014 (Burla et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMOL (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010).Fig. 1. Reaction scheme for the preparation of the title compound. | |
Fig. 2. The molecular structures of the two independent molecules in the title compound showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level. | |
Fig. 3. Superimposition of the two independent molecules. Molecule A is shown in blue and B in red. The molecules have been superimposed such that the benzene rings are overlapped. | |
Fig. 4. A view of the supramolecular chain sustained by O—H···O and N—H···O hydrogen bonds (orange and blue dashed lines, respectively) and aligned along the a axis in the crystal packing. | |
Fig. 5. A view in projection down the a axis of the unit-cell contents. The O—H···O, N—H···O and C—H···O interactions are shown as orange, blue and purple dashed lines, respectively. |
C10H11NO2 | Dx = 1.379 Mg m−3 |
Mr = 177.20 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, P212121 | Cell parameters from 5937 reflections |
a = 6.2846 (1) Å | θ = 3.2–74.2° |
b = 13.8914 (1) Å | µ = 0.79 mm−1 |
c = 19.5592 (2) Å | T = 100 K |
V = 1707.56 (3) Å3 | Prism, colourless |
Z = 8 | 0.35 × 0.25 × 0.15 mm |
F(000) = 752 |
Agilent SuperNova CCD diffractometer | 3336 reflections with I > 2σ(I) |
Radiation source: SuperNova (Cu) X-ray Source | Rint = 0.011 |
ω scans | θmax = 74.3°, θmin = 3.9° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | h = −7→7 |
Tmin = 0.882, Tmax = 1.000 | k = −17→17 |
6258 measured reflections | l = −14→24 |
3358 independent reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.026 | w = 1/[σ2(Fo2) + (0.0483P)2 + 0.1971P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.070 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.15 e Å−3 |
3358 reflections | Δρmin = −0.29 e Å−3 |
251 parameters | Absolute structure: Flack x determined using 1359 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
4 restraints | Absolute structure parameter: −0.05 (6) |
C10H11NO2 | V = 1707.56 (3) Å3 |
Mr = 177.20 | Z = 8 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 6.2846 (1) Å | µ = 0.79 mm−1 |
b = 13.8914 (1) Å | T = 100 K |
c = 19.5592 (2) Å | 0.35 × 0.25 × 0.15 mm |
Agilent SuperNova CCD diffractometer | 3358 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 3336 reflections with I > 2σ(I) |
Tmin = 0.882, Tmax = 1.000 | Rint = 0.011 |
6258 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.070 | Δρmax = 0.15 e Å−3 |
S = 1.06 | Δρmin = −0.29 e Å−3 |
3358 reflections | Absolute structure: Flack x determined using 1359 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
251 parameters | Absolute structure parameter: −0.05 (6) |
4 restraints |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.62669 (16) | 0.73762 (7) | 0.18705 (5) | 0.0180 (2) | |
O2 | 1.32523 (16) | 0.66602 (7) | 0.10231 (5) | 0.0168 (2) | |
H2O | 1.424 (3) | 0.6888 (18) | 0.1273 (11) | 0.049 (7)* | |
N1 | 0.91512 (19) | 0.75379 (8) | 0.11906 (6) | 0.0150 (2) | |
H1N | 0.887 (3) | 0.6996 (10) | 0.0994 (9) | 0.021 (5)* | |
C1 | 0.7850 (2) | 0.78505 (10) | 0.16823 (6) | 0.0144 (3) | |
C2 | 0.8387 (2) | 0.87911 (10) | 0.20099 (7) | 0.0156 (3) | |
C3 | 0.6905 (2) | 0.92359 (11) | 0.24371 (7) | 0.0195 (3) | |
H3 | 0.5548 | 0.8950 | 0.2507 | 0.023* | |
C4 | 0.7411 (3) | 1.00942 (11) | 0.27601 (8) | 0.0228 (3) | |
H4 | 0.6397 | 1.0401 | 0.3047 | 0.027* | |
C5 | 0.9411 (3) | 1.05064 (11) | 0.26623 (8) | 0.0212 (3) | |
H5 | 0.9764 | 1.1091 | 0.2887 | 0.025* | |
C6 | 1.0884 (2) | 1.00671 (10) | 0.22384 (7) | 0.0187 (3) | |
H6 | 1.2240 | 1.0355 | 0.2172 | 0.022* | |
C7 | 1.0392 (2) | 0.92024 (10) | 0.19065 (7) | 0.0158 (3) | |
C8 | 1.1995 (2) | 0.86671 (10) | 0.14844 (7) | 0.0169 (3) | |
H8A | 1.2810 | 0.8226 | 0.1784 | 0.020* | |
H8B | 1.3008 | 0.9132 | 0.1282 | 0.020* | |
C9 | 1.0952 (2) | 0.80877 (10) | 0.09148 (7) | 0.0153 (3) | |
H9 | 1.0405 | 0.8544 | 0.0561 | 0.018* | |
C10 | 1.2538 (2) | 0.74041 (10) | 0.05779 (7) | 0.0163 (3) | |
H10A | 1.1863 | 0.7108 | 0.0172 | 0.020* | |
H10B | 1.3783 | 0.7779 | 0.0419 | 0.020* | |
O3 | 0.10908 (16) | 0.52866 (7) | −0.04188 (5) | 0.0200 (2) | |
O4 | 0.80454 (17) | 0.57641 (7) | 0.04790 (5) | 0.0183 (2) | |
H4O | 0.904 (3) | 0.5612 (18) | 0.0200 (11) | 0.050 (7)* | |
N2 | 0.3944 (2) | 0.49397 (8) | 0.02382 (6) | 0.0165 (2) | |
H2N | 0.373 (4) | 0.5458 (11) | 0.0481 (9) | 0.028 (5)* | |
C11 | 0.2649 (2) | 0.47641 (10) | −0.02887 (7) | 0.0160 (3) | |
C12 | 0.3141 (2) | 0.39062 (10) | −0.07222 (7) | 0.0174 (3) | |
C13 | 0.1653 (2) | 0.35932 (11) | −0.12001 (7) | 0.0217 (3) | |
H13 | 0.0327 | 0.3916 | −0.1242 | 0.026* | |
C14 | 0.2107 (3) | 0.28085 (12) | −0.16165 (7) | 0.0241 (3) | |
H14 | 0.1092 | 0.2591 | −0.1941 | 0.029* | |
C15 | 0.4058 (3) | 0.23446 (11) | −0.15537 (8) | 0.0249 (3) | |
H15 | 0.4370 | 0.1805 | −0.1835 | 0.030* | |
C16 | 0.5553 (3) | 0.26632 (11) | −0.10831 (8) | 0.0230 (3) | |
H16 | 0.6883 | 0.2342 | −0.1047 | 0.028* | |
C17 | 0.5124 (2) | 0.34507 (10) | −0.06620 (7) | 0.0188 (3) | |
C18 | 0.6750 (2) | 0.38637 (10) | −0.01815 (8) | 0.0208 (3) | |
H18A | 0.7610 | 0.4350 | −0.0428 | 0.025* | |
H18B | 0.7720 | 0.3344 | −0.0031 | 0.025* | |
C19 | 0.5744 (2) | 0.43317 (10) | 0.04445 (7) | 0.0179 (3) | |
H19 | 0.5197 | 0.3811 | 0.0751 | 0.022* | |
C20 | 0.7337 (2) | 0.49417 (10) | 0.08474 (7) | 0.0194 (3) | |
H20A | 0.6665 | 0.5155 | 0.1279 | 0.023* | |
H20B | 0.8583 | 0.4539 | 0.0966 | 0.023* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0137 (5) | 0.0198 (5) | 0.0204 (5) | −0.0022 (4) | 0.0008 (4) | −0.0006 (4) |
O2 | 0.0153 (5) | 0.0148 (5) | 0.0203 (5) | 0.0004 (4) | −0.0012 (4) | −0.0004 (4) |
N1 | 0.0141 (5) | 0.0138 (5) | 0.0171 (5) | −0.0010 (4) | −0.0001 (4) | −0.0022 (4) |
C1 | 0.0131 (6) | 0.0157 (6) | 0.0145 (6) | 0.0020 (5) | −0.0029 (5) | 0.0016 (5) |
C2 | 0.0162 (7) | 0.0161 (6) | 0.0146 (6) | 0.0009 (5) | −0.0017 (5) | 0.0005 (5) |
C3 | 0.0163 (7) | 0.0229 (7) | 0.0193 (6) | 0.0007 (6) | 0.0009 (6) | −0.0021 (5) |
C4 | 0.0222 (7) | 0.0242 (7) | 0.0219 (7) | 0.0035 (6) | 0.0021 (6) | −0.0061 (6) |
C5 | 0.0247 (8) | 0.0180 (7) | 0.0210 (7) | −0.0005 (6) | −0.0045 (6) | −0.0050 (5) |
C6 | 0.0193 (7) | 0.0172 (6) | 0.0196 (7) | −0.0026 (6) | −0.0027 (5) | −0.0004 (5) |
C7 | 0.0170 (7) | 0.0154 (6) | 0.0152 (6) | 0.0011 (5) | −0.0021 (5) | 0.0015 (5) |
C8 | 0.0131 (6) | 0.0162 (6) | 0.0216 (7) | −0.0017 (5) | 0.0005 (6) | −0.0017 (5) |
C9 | 0.0137 (6) | 0.0153 (6) | 0.0167 (6) | 0.0003 (5) | 0.0015 (5) | 0.0009 (5) |
C10 | 0.0158 (6) | 0.0179 (6) | 0.0152 (6) | 0.0013 (5) | 0.0013 (5) | 0.0013 (5) |
O3 | 0.0151 (5) | 0.0225 (5) | 0.0225 (5) | 0.0022 (4) | −0.0001 (4) | −0.0020 (4) |
O4 | 0.0162 (5) | 0.0161 (5) | 0.0227 (5) | −0.0004 (4) | 0.0016 (4) | −0.0021 (4) |
N2 | 0.0163 (6) | 0.0150 (5) | 0.0183 (5) | 0.0013 (5) | 0.0003 (5) | −0.0032 (4) |
C11 | 0.0143 (6) | 0.0167 (6) | 0.0172 (6) | −0.0033 (5) | 0.0034 (5) | 0.0004 (5) |
C12 | 0.0179 (7) | 0.0169 (6) | 0.0174 (6) | −0.0030 (5) | 0.0034 (5) | −0.0017 (5) |
C13 | 0.0191 (7) | 0.0253 (7) | 0.0206 (7) | −0.0040 (6) | 0.0026 (6) | −0.0014 (6) |
C14 | 0.0275 (8) | 0.0260 (7) | 0.0187 (7) | −0.0089 (6) | 0.0018 (6) | −0.0036 (6) |
C15 | 0.0348 (9) | 0.0187 (6) | 0.0212 (7) | −0.0057 (7) | 0.0083 (6) | −0.0046 (6) |
C16 | 0.0250 (7) | 0.0173 (7) | 0.0267 (7) | 0.0007 (6) | 0.0057 (6) | −0.0022 (6) |
C17 | 0.0195 (7) | 0.0159 (6) | 0.0210 (6) | −0.0020 (5) | 0.0034 (5) | −0.0006 (5) |
C18 | 0.0156 (7) | 0.0180 (6) | 0.0288 (7) | 0.0018 (5) | −0.0001 (6) | −0.0040 (6) |
C19 | 0.0169 (6) | 0.0153 (6) | 0.0215 (7) | 0.0011 (5) | −0.0018 (5) | 0.0019 (5) |
C20 | 0.0185 (7) | 0.0200 (6) | 0.0198 (6) | −0.0005 (6) | −0.0026 (5) | 0.0005 (5) |
O1—C1 | 1.2486 (17) | O3—C11 | 1.2454 (18) |
O2—C10 | 1.4239 (16) | O4—C20 | 1.4220 (17) |
O2—H2O | 0.849 (13) | O4—H4O | 0.855 (13) |
N1—C1 | 1.3351 (18) | N2—C11 | 1.3356 (18) |
N1—C9 | 1.4680 (17) | N2—C19 | 1.4682 (18) |
N1—H1N | 0.863 (12) | N2—H2N | 0.872 (12) |
C1—C2 | 1.4939 (18) | C11—C12 | 1.4949 (18) |
C2—C3 | 1.396 (2) | C12—C13 | 1.392 (2) |
C2—C7 | 1.398 (2) | C12—C17 | 1.402 (2) |
C3—C4 | 1.386 (2) | C13—C14 | 1.390 (2) |
C3—H3 | 0.9500 | C13—H13 | 0.9500 |
C4—C5 | 1.395 (2) | C14—C15 | 1.391 (2) |
C4—H4 | 0.9500 | C14—H14 | 0.9500 |
C5—C6 | 1.385 (2) | C15—C16 | 1.388 (2) |
C5—H5 | 0.9500 | C15—H15 | 0.9500 |
C6—C7 | 1.400 (2) | C16—C17 | 1.396 (2) |
C6—H6 | 0.9500 | C16—H16 | 0.9500 |
C7—C8 | 1.4997 (19) | C17—C18 | 1.502 (2) |
C8—C9 | 1.5227 (18) | C18—C19 | 1.524 (2) |
C8—H8A | 0.9900 | C18—H18A | 0.9900 |
C8—H8B | 0.9900 | C18—H18B | 0.9900 |
C9—C10 | 1.5263 (19) | C19—C20 | 1.5303 (19) |
C9—H9 | 1.0000 | C19—H19 | 1.0000 |
C10—H10A | 0.9900 | C20—H20A | 0.9900 |
C10—H10B | 0.9900 | C20—H20B | 0.9900 |
C10—O2—H2O | 108.1 (18) | C20—O4—H4O | 110.7 (17) |
C1—N1—C9 | 124.60 (12) | C11—N2—C19 | 125.20 (12) |
C1—N1—H1N | 118.7 (14) | C11—N2—H2N | 118.6 (14) |
C9—N1—H1N | 116.5 (14) | C19—N2—H2N | 116.2 (14) |
O1—C1—N1 | 121.92 (13) | O3—C11—N2 | 122.02 (13) |
O1—C1—C2 | 121.01 (12) | O3—C11—C12 | 120.76 (12) |
N1—C1—C2 | 117.06 (12) | N2—C11—C12 | 117.21 (12) |
C3—C2—C7 | 120.47 (13) | C13—C12—C17 | 120.82 (13) |
C3—C2—C1 | 119.55 (13) | C13—C12—C11 | 119.41 (13) |
C7—C2—C1 | 119.94 (12) | C17—C12—C11 | 119.73 (13) |
C4—C3—C2 | 120.03 (14) | C14—C13—C12 | 120.04 (15) |
C4—C3—H3 | 120.0 | C14—C13—H13 | 120.0 |
C2—C3—H3 | 120.0 | C12—C13—H13 | 120.0 |
C3—C4—C5 | 119.83 (14) | C13—C14—C15 | 119.50 (14) |
C3—C4—H4 | 120.1 | C13—C14—H14 | 120.3 |
C5—C4—H4 | 120.1 | C15—C14—H14 | 120.3 |
C6—C5—C4 | 120.26 (13) | C16—C15—C14 | 120.51 (14) |
C6—C5—H5 | 119.9 | C16—C15—H15 | 119.7 |
C4—C5—H5 | 119.9 | C14—C15—H15 | 119.7 |
C5—C6—C7 | 120.54 (14) | C15—C16—C17 | 120.70 (15) |
C5—C6—H6 | 119.7 | C15—C16—H16 | 119.7 |
C7—C6—H6 | 119.7 | C17—C16—H16 | 119.7 |
C2—C7—C6 | 118.86 (13) | C16—C17—C12 | 118.42 (14) |
C2—C7—C8 | 118.83 (12) | C16—C17—C18 | 122.47 (14) |
C6—C7—C8 | 122.17 (13) | C12—C17—C18 | 119.00 (12) |
C7—C8—C9 | 112.08 (12) | C17—C18—C19 | 112.53 (12) |
C7—C8—H8A | 109.2 | C17—C18—H18A | 109.1 |
C9—C8—H8A | 109.2 | C19—C18—H18A | 109.1 |
C7—C8—H8B | 109.2 | C17—C18—H18B | 109.1 |
C9—C8—H8B | 109.2 | C19—C18—H18B | 109.1 |
H8A—C8—H8B | 107.9 | H18A—C18—H18B | 107.8 |
N1—C9—C8 | 109.74 (11) | N2—C19—C18 | 110.14 (11) |
N1—C9—C10 | 109.78 (11) | N2—C19—C20 | 109.10 (11) |
C8—C9—C10 | 111.33 (11) | C18—C19—C20 | 112.23 (12) |
N1—C9—H9 | 108.6 | N2—C19—H19 | 108.4 |
C8—C9—H9 | 108.6 | C18—C19—H19 | 108.4 |
C10—C9—H9 | 108.6 | C20—C19—H19 | 108.4 |
O2—C10—C9 | 113.17 (11) | O4—C20—C19 | 112.88 (11) |
O2—C10—H10A | 108.9 | O4—C20—H20A | 109.0 |
C9—C10—H10A | 108.9 | C19—C20—H20A | 109.0 |
O2—C10—H10B | 108.9 | O4—C20—H20B | 109.0 |
C9—C10—H10B | 108.9 | C19—C20—H20B | 109.0 |
H10A—C10—H10B | 107.8 | H20A—C20—H20B | 107.8 |
C9—N1—C1—O1 | 175.75 (12) | C19—N2—C11—O3 | 176.74 (13) |
C9—N1—C1—C2 | −5.26 (19) | C19—N2—C11—C12 | −3.2 (2) |
O1—C1—C2—C3 | −12.24 (19) | O3—C11—C12—C13 | −11.1 (2) |
N1—C1—C2—C3 | 168.76 (13) | N2—C11—C12—C13 | 168.84 (13) |
O1—C1—C2—C7 | 165.51 (12) | O3—C11—C12—C17 | 166.40 (13) |
N1—C1—C2—C7 | −13.49 (18) | N2—C11—C12—C17 | −13.68 (19) |
C7—C2—C3—C4 | 0.3 (2) | C17—C12—C13—C14 | 1.2 (2) |
C1—C2—C3—C4 | 178.05 (13) | C11—C12—C13—C14 | 178.68 (13) |
C2—C3—C4—C5 | −0.6 (2) | C12—C13—C14—C15 | −0.4 (2) |
C3—C4—C5—C6 | 0.7 (2) | C13—C14—C15—C16 | −0.4 (2) |
C4—C5—C6—C7 | −0.4 (2) | C14—C15—C16—C17 | 0.3 (2) |
C3—C2—C7—C6 | 0.0 (2) | C15—C16—C17—C12 | 0.5 (2) |
C1—C2—C7—C6 | −177.76 (12) | C15—C16—C17—C18 | −175.52 (14) |
C3—C2—C7—C8 | 175.65 (13) | C13—C12—C17—C16 | −1.3 (2) |
C1—C2—C7—C8 | −2.08 (18) | C11—C12—C17—C16 | −178.75 (13) |
C5—C6—C7—C2 | 0.1 (2) | C13—C12—C17—C18 | 174.88 (13) |
C5—C6—C7—C8 | −175.46 (13) | C11—C12—C17—C18 | −2.57 (19) |
C2—C7—C8—C9 | 33.21 (17) | C16—C17—C18—C19 | −151.24 (14) |
C6—C7—C8—C9 | −151.25 (13) | C12—C17—C18—C19 | 32.74 (18) |
C1—N1—C9—C8 | 35.96 (18) | C11—N2—C19—C18 | 32.98 (18) |
C1—N1—C9—C10 | 158.62 (12) | C11—N2—C19—C20 | 156.58 (12) |
C7—C8—C9—N1 | −47.52 (15) | C17—C18—C19—N2 | −45.45 (16) |
C7—C8—C9—C10 | −169.26 (11) | C17—C18—C19—C20 | −167.21 (12) |
N1—C9—C10—O2 | −55.30 (15) | N2—C19—C20—O4 | −55.94 (16) |
C8—C9—C10—O2 | 66.42 (15) | C18—C19—C20—O4 | 66.41 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···O1i | 0.85 (1) | 1.86 (1) | 2.7066 (14) | 176 (3) |
O4—H4O···O3i | 0.86 (1) | 1.83 (1) | 2.6808 (15) | 178 (3) |
N1—H1N···O4 | 0.86 (1) | 2.05 (1) | 2.9141 (15) | 176 (2) |
N2—H2N···O2ii | 0.87 (1) | 2.00 (1) | 2.8737 (15) | 179 (2) |
C4—H4···O2iii | 0.95 | 2.53 | 3.2512 (18) | 132 |
C8—H8A···O1i | 0.99 | 2.48 | 3.3157 (16) | 142 |
C18—H18A···O3i | 0.99 | 2.55 | 3.4007 (16) | 145 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) −x+2, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···O1i | 0.849 (13) | 1.859 (13) | 2.7066 (14) | 176 (3) |
O4—H4O···O3i | 0.855 (13) | 1.826 (13) | 2.6808 (15) | 178 (3) |
N1—H1N···O4 | 0.863 (12) | 2.053 (12) | 2.9141 (15) | 175.7 (19) |
N2—H2N···O2ii | 0.872 (12) | 2.002 (12) | 2.8737 (15) | 179.0 (19) |
C4—H4···O2iii | 0.95 | 2.53 | 3.2512 (18) | 132 |
C8—H8A···O1i | 0.99 | 2.48 | 3.3157 (16) | 142 |
C18—H18A···O3i | 0.99 | 2.55 | 3.4007 (16) | 145 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) −x+2, y+1/2, −z+1/2. |
Acknowledgements
The Brazilian agencies CNPq (306121/2013-2 to IC, 117695/2014-9 to CLH and 305626/2013-2 to JZS), CAPES and FAPESP are acknowledged for financial support.
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